3158+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Leesburg

Leesburg pickleball Stays, Resort Rentals, & Homes

About Leesburg Vacation Rentals

Discover over 3158 amazing vacation rental options in Leesburg with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Leesburg.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 1517.27 ft², with prices averaging US $206 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Leesburg.

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Top Pickleball-Ready Accommodation Types in Leesburg

Type Count
Vacation Homes 2339
Villas 447
Cottages 124
Holiday Apartments 102

Use these Quick Filters to Find a Vacation Rental in Leesburg

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Leesburg with PickleTrip™.

Weather in Leesburg, FL

View the weather forecast for Leesburg before booking your Leesburg Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Leesburg, FL

PickleTrip offers a large selection of top attractions around Leesburg . Research things to do on your vacation before you visit Leesburg.


The Villages Market Square
Spanish Springs Town Square
Lake Dora
Venetian Gardens
TableTop Team Trivia
Mission Inn Golf Resort - El Campeon
Gilbert Park
Country Club of Mount Dora
Donnelly Park
Florida National Cemetery
Continental Country Club
Eustis Village Shopping Center
Mount Dora Area Chamber of Commerce
Harbor Hills Country Club
ViaPort Florida
Orange Blossom Hills Golf & Country Club
Black Bear Golf Club
Lake Okahumpka Park
Eustis Square
Renninger's Antique Center

Other Places to Stay in Leesburg, FL


Sumter County 1,213 Properties
Lake County 1,168 Properties
The Villages 785 Properties
Wildwood 351 Properties
Mount Dora 226 Properties
Bushnell 112 Properties
Tavares 104 Properties
Lady Lake 69 Properties
Lake Deaton 53 Properties
Eustis 43 Properties
Summerfield 43 Properties
Duval 35 Properties

Frequently Asked Questions About Leesburg?

What are the top vacation rentals, resorts, and hotels in Leesburg with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Leesburg. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Leesburg!

How many pickleball-ready properties have private pools in Leesburg?

Discover 164 accommodations with private or nearby pickleball courts in Leesburg. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Leesburg is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Leesburg? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Leesburg?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 3158 properties listed in Leesburg in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (16) 
Neighborhood Property Count
Duval Vacation Rentals in Leesburg, Florida 35
Virginia Trace Vacation Rentals in Leesburg, Florida 27
Lynnhaven Vacation Rentals in Leesburg, Florida 26
Liberty Park Vacation Rentals in Leesburg, Florida 876
Mallory Square Vacation Rentals in Leesburg, Florida 842
Lake Sumter Landing Vacation Rentals in Leesburg, Florida 1010
Fernandina Vacation Rentals in Leesburg, Florida 759
Del Mar Vacation Rentals in Leesburg, Florida 496
Caroline Vacation Rentals in Leesburg, Florida 834
Collier Vacation Rentals in Leesburg, Florida 735
Charlotte Vacation Rentals in Leesburg, Florida 615
Sabal Chase Vacation Rentals in Leesburg, Florida 921
Hemingway Vacation Rentals in Leesburg, Florida 789
Piedmont Vacation Rentals in Leesburg, Florida 431
Springdale Vacation Rentals in Leesburg, Florida 433
Bonita Vacation Rentals in Leesburg, Florida 823

People Also Ask

There are 3158 Leesburg, FL Vacation Rentals

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